Carbazole Annulation via Cascade Nucleophilic Addition–Cyclization Involving 2-(Silyloxy)pentadienyl Cation
Publication type: Journal Article
Publication date: 2016-06-06
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
27265237
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
We report a new strategy toward the synthesis of highly functionalized carbazoles via 2-(silyloxy)pentadienyl cation intermediates, which were generated upon ionization of vinyl-substituted α-hydroxy silyl enol ethers under Brønsted acid catalysis. These electrophilic species were found to readily undergo cascade reactions with substituted indoles to generate carbazole molecular scaffolds in good yields via a sequence of regioselective nucleophilic addition, followed by intramolecular dehydrative cyclization.
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36
Total citations:
36
Citations from 2024:
6
(16.67%)
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GOST
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Stepherson J. R. et al. Carbazole Annulation via Cascade Nucleophilic Addition–Cyclization Involving 2-(Silyloxy)pentadienyl Cation // Organic Letters. 2016. Vol. 18. No. 12. pp. 3002-3005.
GOST all authors (up to 50)
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Stepherson J. R., Ayala C. E., Tugwell T. H., Henry J. L., Fronczek F. R., Kartika R. Carbazole Annulation via Cascade Nucleophilic Addition–Cyclization Involving 2-(Silyloxy)pentadienyl Cation // Organic Letters. 2016. Vol. 18. No. 12. pp. 3002-3005.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.6b01376
UR - https://doi.org/10.1021/acs.orglett.6b01376
TI - Carbazole Annulation via Cascade Nucleophilic Addition–Cyclization Involving 2-(Silyloxy)pentadienyl Cation
T2 - Organic Letters
AU - Stepherson, Jacob R.
AU - Ayala, Caitlan E.
AU - Tugwell, Thomas H
AU - Henry, Jeffrey L
AU - Fronczek, Frank R.
AU - Kartika, Rendy
PY - 2016
DA - 2016/06/06
PB - American Chemical Society (ACS)
SP - 3002-3005
IS - 12
VL - 18
PMID - 27265237
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2016_Stepherson,
author = {Jacob R. Stepherson and Caitlan E. Ayala and Thomas H Tugwell and Jeffrey L Henry and Frank R. Fronczek and Rendy Kartika},
title = {Carbazole Annulation via Cascade Nucleophilic Addition–Cyclization Involving 2-(Silyloxy)pentadienyl Cation},
journal = {Organic Letters},
year = {2016},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.6b01376},
number = {12},
pages = {3002--3005},
doi = {10.1021/acs.orglett.6b01376}
}
Cite this
MLA
Copy
Stepherson, Jacob R., et al. “Carbazole Annulation via Cascade Nucleophilic Addition–Cyclization Involving 2-(Silyloxy)pentadienyl Cation.” Organic Letters, vol. 18, no. 12, Jun. 2016, pp. 3002-3005. https://doi.org/10.1021/acs.orglett.6b01376.